4.8 Article

Alkynyliodonium Salt Mediated Alkynylation of Azlactones: Fast Access to Cα-Tetrasubstituted α-Amino Acid Derivatives

Journal

ORGANIC LETTERS
Volume 16, Issue 5, Pages 1326-1329

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol500053c

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Funding

  1. DFG [NA 955/1-1]
  2. Fonds der Chemischen Industrie (Sachkostenzuschuss)
  3. Carl-Zeiss-Stiftung

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An efficient electrophilic alkynylation of azlactones (oxazol-5(4H)-ones) is developed using alkynyl(phenyl)iodonium salts as the electrophilic alkyne source. After remarkably short reaction times, the desired alkyne functionalized azlactones are obtained in 60-97% yield and can be transformed easily into a variety of quaternary alpha-amino acid derivatives.

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